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Photochemical, Metal‐Free Sigmatropic Rearrangement Reactions of Sulfur Ylides
Author(s) -
Yang Zhen,
Guo Yujing,
Koenigs Rene M.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900597
Subject(s) - sigmatropic reaction , chemistry , photochemistry , sulfur , sulfide , photodissociation , catalysis , metal , rearrangement reaction , medicinal chemistry , organic chemistry
Sigmatropic rearrangement reactions constitute one of the most fundamental reactions of carbenes. While state‐of‐the‐art synthetic methods require the use of expensive precious metal catalysts, the application of visible light for the photolysis of α‐aryldiazoacetates is much less investigated and provides an operationally simple entry to carbenes under mild reaction conditions. Herein, we report on blue‐light induced sigmatropic rearrangement reactions of sulfur compounds with α‐aryldiazoacetates. This process, depending on the substitution pattern of the sulfide, opens up formal insertion reactions of carbenes into S−N, S−C, or C−H bonds.